Stacking of Sterically Congested Trifluoromethylated Aromatics in their Crystals – The Role of Weak F···π or F···F Contacts

European journal of organic chemistry : EurJOC 2020(38), 6073-6077 (2020). doi:10.1002/ejoc.202001008

Connecting Electron-Deficient and Electron-Rich Aromatics to Support Intermolecular Interactions in Crystals

Five compounds bearing electron-deficient pentafluorophenyl as well as electron-rich (salicylate or indole) aromatic moieties connected by amide or ester linkages were investigated by X-ray diffraction. In the crystals, various interactions (π–π, lone pair–π) between the different aromatic units are important structure controlling factors in addition to the stronger inter- or intramolecular hydrogen bonds induced by the amide and ester moieties. The hydrogen bonding leads to polymeric and macrocyclic assembly of the molecular building blocks.

Connecting Electron-Deficient and Electron-Rich Aromatics to Support Intermolecular Interactions in Crystals (Eur. J. Org. Chem. 15/2015)

CF3: An Electron-Withdrawing Substituent for Aromatic Anion Acceptors? “Side-On” versus “On-Top” Binding of Halides

The ability of multiple CF3 -substituted arenes to act as acceptors for anions is investigated. The results of quantum-chemical calculations show that a high degree of trifluoromethyl substitution at the aromatic ring results in a positive quadrupole moment. However, depending on the polarizability of the anion and on the substitution at the arene, three different modes of interaction, namely Meisenheimer complex, side-on hydrogen bonding, or anion-π interaction, can occur. Experimentally, the side-on as well as a η(2) -type π-complex are observed in the crystal, whereas in solution only side-on binding is found.

Perfluoro-1,1′-biphenyl and perfluoronaphthalene and their derivatives as π-acceptors for anions

Addition of anions to perfluorinated 1,1′-biphenyl 1 or naphthalene 2 results in a shift of the 19F NMR signals. However, any specific interaction cannot be assigned to this effect. In order to study the interaction in more detail, the salt derivatives 3 and 4 were prepared and studied by single crystal X-ray diffraction revealing weak anion–π interactions in the solid state.

CCDC 1995537: Experimental Crystal Structure Determination

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CCDC 1014201: Experimental Crystal Structure Determination

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CCDC 1995533: Experimental Crystal Structure Determination

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CCDC 1995536: Experimental Crystal Structure Determination

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CCDC 1995534: Experimental Crystal Structure Determination

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CCDC 1036897: Experimental Crystal Structure Determination

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CCDC 1995535: Experimental Crystal Structure Determination

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CCDC 1036896: Experimental Crystal Structure Determination

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CCDC 1036893: Experimental Crystal Structure Determination

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CCDC 1995532: Experimental Crystal Structure Determination

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CCDC 1014200: Experimental Crystal Structure Determination

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CCDC 1036895: Experimental Crystal Structure Determination

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CCDC 1036894: Experimental Crystal Structure Determination

Related Article: Markus Albrecht, Hai Yi, Fangfang Pan, Arto Valkonen and Kari Rissanen|2015|Eur.J.Org.Chem.|2015|3235|doi:10.1002/ejoc.201500175